How long should I go for?You could spend 10 years on Maui and not get your fill. That being said, the bare minimum to enjoy your stay is 4 days on the ground. A week is ideal.

It's possible to do a short trip by leaving early Sunday morning, getting there in the afternoon, and then leaving Thursday night and being back home for shabbos.

Do I need a guide book?Very definitely. Sure you could find most info online, but nothing compares to a good, written-by-a-local, guide book. Maui Revealed is by far the best option, and will possibly be the best $16 you spent on your trip.

There is also an app version available for both iOS and Android for $7.99. The app has all the content of the book, plus navigation, offline maps, and links when applicable. You don't really need both, but some people find it useful to have the book while planning (much easier to use) and the app while on the island (for the maps and navigation).

What about Shabbos?Some authorities hold that there's a dateline issue with Shabbos. The local communities keep Shabbos on Saturday.Definitely ask your LOR before you go - some hold simply that Shabbos is on Saturday, some hold that you have to keep Shabbos on both Friday and Saturday, and some hold that you have to keep D'oreisas on Friday and full Shabbos on Saturday.

If you must keep 2 days, remember that there are many questions that could come up (such as when to light Shabbos candles, how to warm up food, etc.), so make sure to discuss it all with your LOR.

There have been books written about the Chabad opinion of keeping Shabbos only on Saturday. Rabbi Aharon Dovid Gancz gives an absolutely fascinating pilpul on the topic, if you get a chance to attend one please record it (with permission) and upload the video online.

Note that you may run into this issue even if you leave the islands Thursday afternoon, as it may already be considered Shabbos. Ask your LOR.Getting there and getting around:

Air:The main airport is in Kahului, and is designated OGG. The are two other small airports - Kapalua (JHM) in the West Maui Mountains and Hana (HNM) in the east.You could fly directly from the mainland to OGG from (bold is seasonal only):

There are no direct flights from the East coast, so you will stop in one of these cities. Alternately, you could fly directly to Honolulu (HNL) and continue to OGG from there.

Hawaiian and Go fly interisland from HNL, KOA, and LIH, Go, and Island Air flies from HNL. Mokulele flies from HNL and KOA, as well as to Kapalua (JHM), Hana (HNM), Molokai (MKK), Lanai (LNY), and Waimea-Kohala (MUE) on the Big Island.

Alternatively, you can also use 5k AA, 6k UA or 7.5k HA miles each way to fly interisland. You can use 15k DL pesos for a RT interisland. United allows a free stopover on a round-trip, so for instance you can fly HNL-LIH-OGG-HNL for just 12K miles.HA has several tiers, similar to DL, the lowest tier is the only one that's available using partner miles, but with HA miles you can purchase tickets that are otherwise unavailable for additional miles.

Car:A car is necessary on Maui. All major companies have branches, mostly at the airport. There are also some local companies.

Hertz has Gold Choice at the airport. According to National's website there is no Executive Aisle/Selection at the airport, but according to reports there is one, albeit sparse to the point of uselessness. Also check out www.discounthawaiicarrental.com - they book from the major brands, and are worth a try. Costco Travel very often has great prices too.

Make sure to check your reservations often, as prices tend to drop a few weeks before pickup. If it does, make a new reservation and only then cancel your original one.

There's nothing like a convertible on Maui (especially on the Road to Hana). A 4WD is not really necessary, however some people feel more comfortable in one on the 'other side' of the Road to Hana and the hairy parts of Kahekill Hwy (east of the blowhole).

Air Maui will mail you a nice free paper map of the island - click here to request it. It usually takes a week or two to arrive.Where to stay:

The two most popular area to stay are on the West side (Lahaina, Ka'anapali, Kapalua) and the South side (Wailea, Kihei), due to the better weather there. The South side could sometimes get windy in the winter, though. There are also many places to rent Upcountry (Kula, Pukalani), where the air is cooler and the views smashing (but farther from the beach).

Hyatt Category 5. The Hyatt advertises having Kosher food. In the past, these meals came from Oahu Kosher (Chabad in Honolulu). However, in Dec 2016 they claimed the meals were prepared by the Chabad of Maui, while in actuality they were prepared by a reform temple (story explained at the bottom of this post), which is still true as of Feb 2017.

There are countless condos, timeshares, or villas available to rent on the island. The advantages are that you get more for your money - a couple of bedrooms, living/dining rooms, and a full kitchen. There will usually be a pool, sometimes even a private one. Additionally, they're often cheaper than a hotel. There are many places to find them -HomeAway MauiVRBO MauiAirbnb Maui

What to do:

Beaches:There are countless beaches on Maui, and all are public. Most offer amazing snorkeling. The East and South side beaches are safe for swimming / snorkeling year round, while some North and West beaches could be deadly in winter. Here are some popular ones, in no particular order:

Hiking:There are a tremendous amount of great hikes on Maui. Check the Maui Revealed book for detailed info on all of them, with maps, difficulty ratings, etc. These are just a few which are discussed in this thread:

An amazing hike into the crater from the upper visitors center. Quite challenging due to the constant downhill on a loose cinder trail. Amazing views unlike anything on the island, and no shade. The entire trail takes all day, but most people take it only partway in. Go as far as you like and remember that the way back is a constant uphill and will take twice as long. Bring lots of water.

Pipiwai Trail

Hana

One of the nicest trail on Maui. A bit past Hana, just before the Seven Sacred Pools. The hike goes through the jungle, past banyan trees and a 200-foot waterfall, and through a bamboo forest (this is the highlight for most people). The trail ends at the amazing 400-foot Waimoku Falls. Give this hike a couple of hours.

Lava Field

South Maui

At the end of the road, past the Ahihi-Kinau Natural Area Reserve. This is an amazing and relatively difficult hike. You will be walking on sharp, loose lava rocks the entire time, but the views are smashing and the terrain interesting. Great views of a particularly wild stretch of ocean, interesting pools (not swimmable), and ends in a glorious (and generally empty) beach if you brave it till the end. Do the loop - hug the coast on the way out, and take the Kings Highway back. See Maui Revealed for all the details.

A few companies offer this; Blue Hawaiian is generally considered to be the best. There are different routes to choose from - keep in mind that the ones going to Haleakala don't actually go into the crater. This is not as recommended on Maui as it is on other islands, since the entire island is pretty much easily accessible so you won't go anywhere remote or extremely amazing.

Road to Hana

Absolute must-do. Don't get scared off by misinformation and go all the way around - in a way the backside is even more spectacular that the more popular first half. You do NOT need a special car or 4WD; any regular car could do it happily. Best way to do the road is to spend the night in Hana, as that will leave the most time to explore the thousand different things along the road. If you're only going for the day, make sure to be on the road EARLY (7-7:30 the latest).

Haleakala Sunrise

A spectacular event that is not to be missed. You will wake up at the witching hour, it will be freezing cold, and it will be absolutely worth it. Be there at least 45 minutes before the listed sunrise - the earlier the better; they close the upper parking lot when it fills up and you'll have to park at the lower visitor center lot. Dress warmly and bring lots of jackets and blankets. Take the trail to Pakaoao (White Hill) and you'll have the sunrise to yourself (mostly, at least).

'Ohe'o Gulch (Seven Sacred Pools)

Also known as the Seven Sacred Pools, this is in the Hana side of Haleakala National Park. Save your receipt from sunrise; it's valid for three days and will get you in to the pools too. Short hike from the parking lot to the pools, and it's absolutely stunning. Will be absolutely PACKED from around 1PM and on (but still worth it). If you're staying in Hana go early in the morning and it'll be mostly empty.

Snorkling Molokini crater

Countless boat companies will take you out to Molokini. It has the best underwater visibility in the state, sometimes over 100 feet. Somewhat overrated and over-touristed, but generally considered to be worth it.

Kayaking

Biking

Horseback riding

Ziplining

Cruises

Shopping:

Costco in Kahului has some kosher food, as well as the cheapest gas on the island

Great end to a first week, thanks to everyone here that helped me plan an amazing trip!

Friday: went surfing using the "hawaiian surf academy" they had most of us standing on our boards right from the beginning. From there we saw the Banyan tree (first time of many) and from there headed over to the 'iao needle for a great hike off the beaten trail. Spent the rest of the afternoon doing our Walmart and costco shopping and finding some great coffee in a mall also ng the way.

Shabbos: spent with the Shluchim in Maui (thu and Fri night were my only 2 non point redemption nights). Had a very good time but there's not much to see up there as far as Maui goes (they are pretty close to the crater...)

Sunday: we had checked into the hyatt Regency the night before and we kind of took it slow that morning which resulted in us going snorkeling at black Rock, nothing really special but I did see a sea turtle! From there we headed back to Lahaina where we took a submarine by "Atlantis adventures". Once we were done with that we headed to the spectacular blowhole and olivine pools. Try to get there with plenty of time, they are both hikes if you want to do them right.

Monday: checked into the Fairmont, an incredible resort, got 2 free nights with the card and left me questioning myself why I had even bothered with the hyatt in the first place. Went snorkeling in beautiful wailea beach (sadly, no sea turtles) and then took a kayak. From there we headed to Warren and Annabelle's, a throughly entertaining and extremely reasonably priced show. Jewish owners too who come out to mingle with their guests (aka:us) and awesome wait staff too.After the show we checked out downtown Lahaina, there's some amazing stuff over there (check some of the art galleries if you have a chance for a guy who does competition pictures without photoshop).

Tuesday: the road to hana. An amazing drive round at least half of Maui (if you complete the loop as we did). I can't even begin to list all the stops we made, you kind of just read up on it and decide that way. We stopped at one particular waterfall that was a 10 min walk from the road that was completely empty and went swimming there - a much needed relief for my sunburned back - and when you get to Hana, make sure that you see the red sand beach. (don't bring kids there, it can be an "adult" beach).

Wednesday: we slept for about 4 hours then drove up the crater for sunrise. The top peak was closed for repairs (to the parking lot) so we had to stand at one of the lower ones which happened to have a better view we hiked a little, came back to the hotel, packed up, visited another 3 beaches - all diamond in Maui revealed - and headed to the airport (where I'm finishing this TR on my phone).

See some of you in kauai!

P.S. I hope to make it back to Maui someday, if I ever do, I hear Molokini is supposed to have incredible snorkeling.

P.P.S. I would highly recommend getting the "revealed" apps if you have an android device, really helped us find places to go and things to do especially on the road to hana. If you don't want to pay the $7 then trip advisor has a free app that does the same thing, the difference is, the revealed app is written by pros.

Nice trip report. Mine is oddly similar which is why I'll refrain from writing a detailed one. Just some pointers.

Dan has mentioned earlier he suggests doing the whole hana loop and not to just turn around the way you come. I couldn't agree more. The drive is not THAT difficult IMO and it's a gorgeous drive. In fact it was my personal favorite part of the trip. What we did is "stop off" (still a nice drive up the mountain) at haleakala for sunset (which was stunning, and now that I saw that I don't feel guilty not doing sunrise :-)). It will definitely come down to timing but it worked out really well for us and we managed to do an incredible amount in 1 day.

Now I must say I did the loop from olivine pools as well and thoroughly enjoyed it. I know it isn't something many people suggest and I can tell you that the drive is not for the faint hearted. IMO makes the whole Hana loop seem easy. It's much shorter but very very steep winding NARROW (Hana loop roads were wider almost everywhere) roads and again, NOT for someone who isn't confidant in their driving skills (you'll want to turn around once you bump into someone who the other way and find you need to reverse 300 feet down a crazy steep mountain with a thousand foot drop below). You will be rewarded with very beautiful mountain views and the chance to drive through some "real" Hawaiian mountain towns.

Aside from that I stayed in Makena Beach and Golf Resort (priceline) and loved it! Very decent (not the GHK) in looks, but roomy, and great grounds. Access with pool house to service you at the amazing Makena Beach with great snorkeling and swimming right there. Service at the resort was the best I've experienced. No resort/wifi fee and free valet parking (tip suggested). All in all a great resort at very reasonable prices. It's also the Southernmost resort on (past the Four Seasons) and has a great secluded feel to it.

2 nights at the hyatt Regency = 2 nights off a Hyatt card in my name. 2 nights in the fairmont = 2 nights off a fairmont cc in my wife's name. 7 nights at the ghk = 2 suite nights off a Hyatt cc in my wife's name + 5x22k UR points With an upgrade request (didn't have to use any of the upgrades that came with the diamond account I got from getting the Hilton card)

Did name my own price and used a 5% coupon and got it priced out at $190 per night. With no resort fees, free valet parking, and a wonderful amazing hotel in a great location with top notch friendly service, I did very well. Quite glad I didn't burn 22k points a night for the HRM...